Triaryl Carbenium Ion Pair Mediated Electrocatalytic Benzylic C−H Oxygenation in Air

Zhenguo Zhang, Yongheng Lv, Liang Ji, Peng Chen, Shuyan Han, Yufei Zhu, Lanyang Li, Zhenhua Jia*, Teck Peng Loh*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The selective oxidation of benzylic C−H bonds is a pivotal transformation in organic synthesis. Undoubtedly, achieving efficient and highly selective aerobic oxidation of methylarenes to benzaldehydes has been highly challenging due to the propensity of benzaldehyde to undergo overoxidation under typical aerobic conditions. Herein, we propose an innovative approach to address this issue by leveraging electrocatalytic processes, facilitated by ion-pair mediators [Ph3C]+[B(C6F5)4]. By harnessing the power of electrochemistry, we successfully demonstrated the effectiveness of our strategy, which enables the selective oxidation of benzylic C−H bonds in benzylic molecules and toluene derivatives. Notably, our approach exhibited high efficiency, excellent selectivity, and compatibility with various functional groups, underscoring the broad applicability of our methodology.

Original languageEnglish
Article numbere202406588
JournalAngewandte Chemie - International Edition
Volume63
Issue number28
DOIs
Publication statusPublished - Jul 8 2024
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2024 Wiley-VCH GmbH.

ASJC Scopus Subject Areas

  • Catalysis
  • General Chemistry

Keywords

  • benzylic C−H oxygenation
  • electrocatalysis
  • ion pair
  • triaryl carbenium

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